5-Bromo-4,6-dimethyl-3-nitro-2-pyridinylamine → HCID 178433488, compound

HRID 724029Notes

Reaction equation

HRID 724029 reaction equation
[Br:1][C:2]1[C:3]([CH3:13])=[C:4]([N+:10]([O-:12])=[O:11])[C:5](N)=[N:6][C:7]=1[CH3:8].N([O-])=[O:15].[Na+]>FC(F)(F)C(O)=O.O>[Br:1][C:2]1[C:3]([CH3:13])=[C:4]([N+:10]([O-:12])=[O:11])[C:5]([OH:15])=[N:6][C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 36499475-Bromo-4,6-dimethyl-3-nitro-2-pyridinylamineHCID 23668193Sodium Nitrite

Product 1

HCID 178433488HCID 178433488, compound

Reagents, catalysts & solvents 1

HCID 22392675Trifluoroacetic acid waterSolvent

Procedure

To a solution of 5-bromo-4,6-dimethyl-3-nitro-2-pyridinylamine (Heitsch, H.; et al. Bioorg. Med. Chem. 1997, 5, 673., 2.0 g, 8.1 mmol) in trifluoroacetic acid/water (v/v, 2:1, 30 mL) was added sodium nitrite (1.1 g, 16 mmol) in small portions at room temperature, and then the reaction mixture was stirred overnight. The resulting precipitates were collected by filtration, washed with water, and dried under reduced pressure to give 2.2 g (quant.) of the title compound: 1H-NMR (CDCl3) δ 2.53 (3H, s), 2.38 (3H, s).

Workup

  1. customThe resulting precipitates
  2. filtrationwere collected by filtration
  3. washwashed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-c037b52d27e5491bb05c1a91062c4ed9
Source dataset
uspto-grants-2006_11
Patent number
US07141580B2

Reaction notes

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